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Information on EC 5.1.99.3 - allantoin racemase
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5.1.99.3 allantoin racemaseSpecify your search results
Word Map
- 5.1.99.3
-
racemization
- allantoinase
- allantoate
- purine
- urate
-
nonenzymatic
- sephadex
-
uric
- deae-cellulose
-
enantiomer
- utilis
-
klebsiella
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
allantoin racemase, AllR, BFW91_04965, HpxA, HpxA enzyme, KPN_01788, Racemase, allantoin, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AllR
BFW91_04965
HpxA
KPN_01788
Racemase, allantoin
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)(+)-Allantoin = (R)(-)-allantoin
mechanism of enzymic racemization differs from that of non-enzymic racemization
-
(S)(+)-Allantoin = (R)(-)-allantoin
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
racemization
racemization
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
Allantoin racemase
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CAS REGISTRY NUMBER
COMMENTARY
56214-40-5
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-allantoin
(S)-allantoin
-
-
-
-
r
(S)-allantoin
(R)-allantoin
-
-
-
-
r
additional information
?
-
-
stepwise reaction mechanism via a planar unprotonated intermediate. A pair of cysteine residues promotes the stereoinversion of a carbon atom of the ligand without the assistance of cofactors, quantum mechanics/molecular mechanics calculations
-
-
?
additional information
?
-
-
stepwise reaction mechanism via a planar unprotonated intermediate. A pair of cysteine residues promotes the stereoinversion of a carbon atom of the ligand without the assistance of cofactors, quantum mechanics/molecular mechanics calculations
-
-
?
additional information
?
-
Allantoin can undergo racemization through formation of a bicyclic intermediate (faster) or proton exchange at the chiral center (slower). The velocity of the reaction via a bicyclic intermediate is unaffected by the enzyme, whereas the velocity of the reaction via the chiral center is increased by 7 orders of magnitude
-
-
?
additional information
?
-
Allantoin can undergo racemization through formation of a bicyclic intermediate (faster) or proton exchange at the chiral center (slower). The velocity of the reaction via a bicyclic intermediate is unaffected by the enzyme, whereas the velocity of the reaction via the chiral center is increased by 7 orders of magnitude
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.4
(R)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
1.1
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
2.3
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
0.3
(S)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
2.5
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
43
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
57
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
238
(R)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
129
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
183
(S)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
19
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
52
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
595
(R)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
16
(S)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
52
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
610
(S)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20 - 60
-
20°C: about 35% of maximal activity, 30°C: 67% of maximal activity, 60°C: about 85% of maximal activity
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene hpxA is not essential for growth on allantoin
UniProt
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
conversion of allantoin to allantoate is the second of the two ring-opening steps in purine utilization
physiological function
mechanism of racemization involves residue Glu78 acting as a base for the abstraction of the C5 proton of (S)-allantoin and Cys 180 transferring a proton on the opposite side of the allantoin ring. In the stereoinversion of (R)-allantoin, proton abstraction is performed by Cys 180 and reprotonation by Glu 78
physiological function
-
mechanism of racemization involves residue Glu78 acting as a base for the abstraction of the C5 proton of (S)-allantoin and Cys 180 transferring a proton on the opposite side of the allantoin ring. In the stereoinversion of (R)-allantoin, proton abstraction is performed by Cys 180 and reprotonation by Glu 78
-
Show AA Sequence and Transmembrane Helices (381 entries)
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Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexamer
hexamer
-
trimer of dimers, X-ray crystallography
-
hexamer
-
trimer of dimers, X-ray crystallography
-
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 24-34% (w/v) polyethylene glycol 400 with 0.1 M sodium acetate, pH 3.7-4.1
-
in cubic and orthorhombic crystal forms, at 2.10 and 2.15 A resolution, respectively
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C79S/C184S
-
the double mutation leads to total loss of activity
C184S
-
the mutation leads to total loss of activity
-
C79S
-
the mutation leads to total loss of activity
-
C79S/C184S
-
the double mutation leads to total loss of activity
-
C184S
-
the mutation leads to total loss of activity
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C79S
-
the mutation leads to total loss of activity
-
C79S/C184S
-
the double mutation leads to total loss of activity
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E78D
mutant shows diminished catalytic activity affecting kcat and KM for both enantiomers
E78D
-
mutant shows diminished catalytic activity affecting kcat and KM for both enantiomers
-
additional information
additional information
gene insertion mutant, gene hpxA is not essential for growth on allantoin
additional information
-
gene insertion mutant, gene hpxA is not essential for growth on allantoin
additional information
-
gene insertion mutant, gene hpxA is not essential for growth on allantoin
-
additional information
The Pseudomonas protein lacks a cysteine residue (C79 in the Klebsiella pneumoniae AllR sequence) that is essential for the two-base catalytic mechanism of KpAllR. The residue is substituted with glycine
additional information
-
The Pseudomonas protein lacks a cysteine residue (C79 in the Klebsiella pneumoniae AllR sequence) that is essential for the two-base catalytic mechanism of KpAllR. The residue is substituted with glycine
-
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme belong to a 23-gene cluster that encodes the enzymes for utilizing purines as the sole nitrogen source
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Okumura, I.; Yamamoto, T.
Enzymic racemization of allantoin
J. Biochem.
84
891-895
1978
Cyberlindnera jadinii
brenda
Van der Drift, L.; Vogels, G.D.; van der Drift, C.
Allantoin racemase: a new enzyme from Pseudomonas species
Biochim. Biophys. Acta
391
240-248
1975
Comamonas testosteroni, Pseudomonas putida, Pseudomonas fluorescens
brenda
Pope, S.D.; Chen, L.L.; Stewart, V.
Purine utilization by Klebsiella oxytoca M5al: genes for ring-oxidizing and -opening enzymes
J. Bacteriol.
191
1006-1017
2008
Klebsiella oxytoca (B5B0K3), Klebsiella oxytoca, Klebsiella michiganensis M5al (B5B0K3), Klebsiella michiganensis M5al, Klebsiella oxytoca M5al (B5B0K3)
brenda
French, J.B.; Neau, D.B.; Ealick, S.E.
Characterization of the structure and function of Klebsiella pneumoniae allantoin racemase
J. Mol. Biol.
410
447-460
2011
Klebsiella pneumoniae subsp. pneumoniae, Klebsiella pneumoniae subsp. pneumoniae Trevisan MGH78578, Klebsiella pneumoniae subsp. pneumoniae MGH78578
brenda
Cendron, L.; Ramazzina, I.; Puggioni, V.; Maccacaro, E.; Liuzzi, A.; Secchi, A.; Zanotti, G.; Percudani, R.
The structure and function of a microbial allantoin racemase reveal the origin and conservation of a catalytic mechanism
Biochemistry
55
6421-6432
2016
Pseudomonas fluorescens (E3SAZ9), Pseudomonas fluorescens DSM 50090 (E3SAZ9)
brenda
Bovigny, C.; Degiacomi, M.T.; Lemmin, T.; Dal Peraro, M.; Stenta, M.
Reaction mechanism and catalytic fingerprint of allantoin racemase
J. Phys. Chem. B
118
7457-7466
2014
Klebsiella pneumoniae subsp. pneumoniae, Klebsiella pneumoniae subsp. pneumoniae ATCC 700721
brenda
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